sesamin   Click here for help

GtoPdb Ligand ID: 11372

Synonyms: D-(+)-Sesamin | Fagarol
Comment: Sesamin is a natural product that can be extracted from sesame seeds. It has been reported to have antihypertensive action, that is associated with inhibtion of CYP4F2-catalysed 20-HETE (20-hydroxyeicosatetraenoic acid) production [1]. 20-HETE is a vasoactive and natriuretic eicosanoid.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 2
Topological polar surface area 55.38
Molecular weight 354.11
XLogP 2.75
No. Lipinski's rules broken 0
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Canonical SMILES C1Oc2c(O1)cc(cc2)[C@H]1OC[C@H]2[C@@H]1CO[C@@H]2c1ccc2c(c1)OCO2
Isomeric SMILES C1Oc2c(O1)cc(cc2)[C@H]1OC[C@H]2[C@@H]1CO[C@@H]2c1ccc2c(c1)OCO2
InChI InChI=1S/C20H18O6/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2/t13-,14-,19+,20+/m0/s1
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
CYP4F2 Hs Inhibitor Inhibition 6.4 pIC50 - 1
pIC50 6.4 (IC50 3.81x10-7 M) [1]